Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2018-05-29 01:14:12 UTC
Primary IDFDB014716
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNigakihemiacetal B
DescriptionNigakihemiacetal B, also known as neoquassin or simalikahemiacetal a, belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Nigakihemiacetal B is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number76-77-7
Structure
Thumb
Synonyms
SynonymSource
16-Hydroxy-2,12-dimethoxy-picrasa-2,12-diene-1,11-dioneHMDB
NeoquassinHMDB
NeoquassineHMDB
Simalikahemiacetal aHMDB
Picrasa-2,12-diene-1, 11-dione, 16-hydroxy-2,12-dimethoxy-biospider
Picrasa-2,12-diene-1,11-dione, 16-hydroxy-2,12-dimethoxy-biospider
Simalikahemiacetal Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.22ALOGPS
logP2.02ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity105.59 m³·mol⁻¹ChemAxon
Polarizability41.79 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H30O6
IUPAC name11-hydroxy-4,15-dimethoxy-2,6,14,17-tetramethyl-10-oxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-4,14-diene-3,16-dione
InChI IdentifierInChI=1S/C22H30O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15-16,19,23H,8-9H2,1-6H3
InChI KeyBDQNCUODBJZKIY-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(C)C2CC3OC(O)CC4C(C)=C(OC)C(=O)C(C34C)C2(C)C1=O
Average Molecular Weight390.47
Monoisotopic Molecular Weight390.204238692
Classification
Description belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentQuassinoids
Alternative Parents
Substituents
  • Quassinoid
  • Naphthopyran
  • Naphthalene
  • Cyclohexenone
  • Oxane
  • Pyran
  • Ketone
  • Hemiacetal
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 67.67%; H 7.74%; O 24.58%DFC
Melting PointMp 230.5-231°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +41 (CHCl3)DFC
Spectroscopic UV Data[neutral] lmax 255 (e 11650) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-07fr-0119000000-4970cc87b8b1a161cb15JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0114-6206900000-6c3538d2fef74e9739faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-64fade882e8aecbfe9e6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-0019000000-4b3171d6bc60bbc63e59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-3295000000-c8277adab35eba9fa28bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d5eb7feace4bac5dd637JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0009000000-bb40cd6adc919fc1366dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5119000000-72a251218f6f5406c041JSpectraViewer
ChemSpider ID250123
ChEMBL IDNot Available
KEGG Compound IDC08771
Pubchem Compound ID283906
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35922
CRC / DFC (Dictionary of Food Compounds) IDJVF50-X:JVF50-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00003720
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference